Aralkylbenzanthrones and process of preparing them



general formula:'

Patented July '12, 1932 UNITE STATES PATENT oFFics GEORG- xnlinznnm, or FRANKFORT-ON-THE-MAIN-HOCHST, GERMANY, AND ROBERT SEDLMAYR, OF AUSSIG, CZECHOSLOVAKIA, AssIeNoRs 'IO GENERAL nivrm v'n worms, 11m, on NE Ionian. Y., A CORPORATION on DELAWARE Y ARALKYLBENZANTHRONES AND PROCESS on rnnrnnmc renn n No Drawing. Application filed April 1 8, 1929, Serial No. 356,290 and in Germany August 19, 1925. .1

The present invention relates to aralkylbenzanthrones and process of preparing them. i

We have found thatwell-defined and well cr stallized reaction-products "are obtainable by condensing a compound of -the following wherein the Bz l-position marked X, is unsubstituted with a compound of the following general formula:

. "RoH2.Y s wherein Y stands for halogen or hydroxyl and R stands for an aryl group of the henzene series. The condensation is preferably eifected by heating molecular proportions of.

products suitable for the preparationdyestuffs.

The said bodies mayalso be 'obtainedi by benzanthrone or a derivative or substitution product thereof. Inthis case for example sulfuric acid may be used as a condensing agent.

-- .The following examples serve to illu'strate our invention but they are not intended to limit it thereto, the parts being by weight. (1) 46 parts of benzanthrone are heatedto boiling temperature for 10-12 hours with 25' parts of'be nzyl-chlor'ide in 460 parts offtri. chlorobenzene while; adding a small quang of copper powder or zinc chloride:- Thereupon the solvent is driven off by means of water-vapor and the residue is filtered by tity suction, washed withwaterand dried; By

boiling out the mass with alcohol anysman quantity of benzanthrone which may still ad here pass into solution. The residue is crystallized from glacial acetic acid or pyridine.

In this manner the product is obtained in the form of feebly-yellowish needles having their melting point at 187 C. 3 It dissolves in concentrated sulfuric acid to a red solution showing an orange-red fluorescence. Instead of benzyl-chloride substituted benzyl-chlorides,

nitroor chloro benzyl chlorides may also, 'beused.

(2) 23 parts of benzanthrone are dissolved in 250 parts of sulfuric acid of 60 B. To

this solution 16 parts of. paranitrobenzyl-alcohol are added and the whole is stirred for wherein R stands for a substituted or unsubabout 48 hours on the, water-bath. The mass is then ,poured into water, filtered by suction and dried. The reaction product ispurified V (as stated; in Example lyand recrystallized stituted aromatic residue, the benzanthrone f rom a suitable solvent.

(3) 15 parts of 4T8dichlorobenzhth dng;

benzyl chloride are heated, to boiling temperature in the reflux apparatus for 17 hours with a minute quantity of copper-bronze.

After the mass has been worked up (as described in Example 1), it yields, after recrystallization from methylbenzene, fine yellow needles, melting at 207 C. and dissolving in sulfuric acid to a yellowish-brown solution showing a slight fluorescence.

( 1) 46 parts ofbenzanthrone,400 parts of trichlorobenzene, 41 parts of 3-nitro- 1-methoxy-benzyl chloride and 0.4 parts of copper powder are heated to boiling temperature for 12 hours. The product separating after cooling is filtered by suction, washed with alcohol and dried. After recrystallization from glacial acetic acid, the resulting B zl- (3 nitro-4-methoxy) -benzyl-benzanthrone dissolvesinsulfuric acid to a red solution and. V

having its melting point at 227? C.

Weclaim: Y

r 1. The process which comprises heating a compound of the following general formula:

' wherein the Bz leposition, marked X, is u nsubstituted, with a compound of the; following general formula: a v

wherein Y stands for" halogen or hydroxyl and R stands for an aryl group of the benwherein Y stands for zene series inthe presence-of an indifferent organic diluent of a high boiling point and a catalyst.

:2. The process which comprises heating aicompound of the following general formu- .wherein Z stands for hydrogenor chlorine,

with a compound of theifollowing' general formula: V4 r i YX1; V UIH2YV'A -1 v i.

chlorine or hydroxyl and X stands for hydrogen or the methoxy group and-X for hydrogen. or the nitrogroup, in the presence of an indifferenta'ro-j matic diluent of a highjboiling point and acatalyst 1 a 3'. The process whichcomprisesheating'to boiling temperature benzanthrone with wherein It stands for -anaryl group of the benzene series.

7 As new products, the compounds of the following generalformula omQxl wherein Z stands for'hydrogen or chlorine, X for hydrogen or the methoxy group and X for hydrogen or. the nitro group.

1' 8. As a new product, the compound of the following formula:

forming after recrystallization from glacial acetic acid feeblyyellowish needles and dissolving in sulfuric acid to a, red solution showing an orange red fluorescence.

9. 'As a new product, the compound of the following formula: I

forming after recrystallization from'methyl benzene fine yellow needles dissolving in sulfuric acid to a yellowish-brown solution.

10. As a new product, the compound of the following formula:

OEBOOOH;

forming after recrystallization from glacial acetic acid a crystalline powder which dissolves in sulfuric acid to a red solution. In testimony whereof, we aflix our signa- 

